Bipyrimidine fluorene compounds, organic electroluminescent elements, and consumer products

Abstract

Disclosed are a material for an organic electroluminescent element, an organic electroluminescent element, and a consumer product. The organic electroluminescent element comprises an anode, a cathode, and a hole injection layer disposed between the anode and the cathode, wherein the hole injection layer or a hole transport layer comprises a compound represented by general formula (I). The hole injection layer and the charge generation layer disclosed in the application comprise a compound with a bipyrimidinofluorene as a parent nucleus, and can reduce the voltage of an OLED element, improve the efficiency and the life of the element.

Description

Technical Field

[0001] This invention relates to the field of electrochromic technology, and more particularly to a dipyrimidine fluorene compound, an organic electroluminescent element, and a consumer product. Background Technology

[0002] Generally speaking, organic light emission refers to the phenomenon of light emitting when electrical energy is applied to organic materials. Specifically, when an organic layer is placed between the anode and cathode, if a voltage is applied between the two electrodes, holes will be injected from the anode into the organic layer, and electrons will be injected from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons transition to the ground state, they emit light and heat.

[0003] As an effective method for manufacturing organic electroluminescent devices (OLEDs), research has been conducted on replacing single-layer organic layers with multilayer structures. In 1987, Tang proposed an OLED with a stacked structure of functional layers including a hole layer and a light-emitting layer. Most currently used OLEDs consist of: a substrate, an anode, a hole injection layer that receives holes from the anode, a hole transport layer that transports holes, a light-emitting layer that allows holes and electrons to recombine and emit light, an electron transport layer that transports electrons, an electron injection layer that receives electrons from the cathode, and a cathode. The rationale for fabricating OLEDs with multiple layers is that, due to the different movement speeds of holes and electrons, if appropriate hole injection and transport layers, as well as electron transport and electron injection layers, are fabricated, holes and electrons can be effectively transported, achieving a balance between holes and electrons within the device and improving exciton utilization.

[0004] In OLED devices, the hole injection layer (HIL) facilitates hole injection from the ITO anode to the organic layer. To achieve low device drive voltages, a minimal charge injection barrier from the anode is crucial. Various HIL materials have been developed, such as triarylamine compounds with shallow HOMO levels, highly electron-deficient heterocyclic compounds, and triarylamine compounds doped with p-type conductive dopants. Developing higher-performance HIL materials is essential to improving OLED performance, such as longer device lifetime, higher efficiency, and lower voltage.

[0005] Therefore, in order to overcome the technical problems mentioned above and further improve the characteristics of organic electroluminescent devices, there is a continued demand for the development of more stable and effective materials that can be used as hole injection and transport materials in organic electroluminescent devices. Summary of the Invention

[0006] This invention aims to improve the voltage, efficiency, and lifetime of OLEDs by using a hole injection layer comprising a compound with a dipyrimidine fluorene core. Furthermore, a charge injection layer comprising a compound with a dipyrimidine fluorene core is also provided, which can be used as a p-type charge generation layer in a tandem OLED structure to further improve the voltage, efficiency, and lifetime of the OLED.

[0007] According to one embodiment of the present invention, a dipyrimidine fluorene compound is disclosed, the general formula of which is as follows:

[0008]

[0009] Among them, X 1 X 2 X 3 X 4 Each independently selected from CR 0 Or N, and in X 1 X 2 X 3 X 4 At least two of them are N;

[0010] R 1 R 2 Each time they appear, the same or different ones represent electron-withdrawing groups;

[0011] R 0 R 3 R 4 Each is independently selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted C1-C. 40 Alkyl, substituted or unsubstituted C3-C 40 Branched alkyl or cycloalkyl groups, substituted or unsubstituted C1-C 40 heteroalkyl, substituted or unsubstituted C2-C 40 alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C3-C 40 alkylsilyl, substituted or unsubstituted C6-C 60 arylsilyl, substituted or unsubstituted, having C0-C 40 The amino group, or the substituted or unsubstituted C2-C 60 The group consisting of heterocyclic aryl, acyl, carbonyl, carboxylic acid, ester, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, and phosphoxy groups, wherein two or more adjacent groups may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, the formed rings containing or not containing one or more heteroatoms N, P, B, O, or S.

[0012] In this specification, "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle formed by the combination of adjacent groups.

[0013] According to another embodiment of the present invention, a material for an organic electroluminescent element is also disclosed, comprising a compound represented by the general formula (I) described above.

[0014] According to another embodiment of the present invention, a series organic electroluminescent element is also disclosed, which includes an anode, a cathode, and a plurality of stacked layers disposed between the anode and the cathode, each stacked layer including at least one light-emitting layer, and a charge-generating layer disposed between each adjacent pair of stacked layers, the charge-generating layer including a p-type charge-generating layer and an n-type charge-generating layer, wherein the p-type charge-generating layer contains a compound represented by the general formula (I) described above.

[0015] According to another embodiment of the present invention, a consumer product is also disclosed, comprising the above-described organic electroluminescent element or the above-described series organic electroluminescent element.

[0016] The hole injection layer and charge generation layer disclosed in this invention comprise compounds with or composed of dipyrimidine fluorene as the core, which can reduce the voltage of OLED devices and improve the efficiency and lifespan of the devices. Attached Figure Description

[0017] Figure 1 This is a schematic diagram of the organic light-emitting device 100 provided by the present invention, comprising a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be manufactured by sequentially depositing the described layers.

[0018] Figure 2 This is a schematic diagram of a tandem organic light-emitting device 500 provided by the present invention; it includes a substrate 101, an anode 110, a first unit 100, a charge-generating layer 300, a second unit 200, and a cathode 290. The first unit 100 includes a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, and an electron transport layer 170. The second unit 200 includes a hole injection layer 220, a hole transport layer 230, an electron blocking layer 240, a light-emitting layer 250, a hole blocking layer 260, an electron transport layer 270, and an electron injection layer 280. The charge-generating layer 300 includes an N-type charge-generating layer 310 and a P-type charge-generating layer 320. The device 500 can be manufactured by sequentially depositing the described layers.

[0019] Figure 3 This is a schematic diagram of another tandem organic light-emitting device 600 provided by the present invention, comprising a substrate 101, an anode 110, a first unit 100, a charge generation layer 300, a second unit 200, an encapsulation layer 102, and a cathode 290. The first unit 100 includes a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, and an electron transport layer 170. The second unit 200 includes a hole injection layer 220, a hole transport layer 230, an electron blocking layer 240, a light-emitting layer 250, a hole blocking layer 260, an electron transport layer 270, and an electron injection layer 280. The charge generation layer 300 includes an N-type charge generation layer 310 and a P-type charge generation layer 320. Detailed Implementation

[0020] The present invention will be further described in detail below with reference to specific embodiments, but it is not intended to limit the scope of the present invention.

[0021] OLEDs can be manufactured on various substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is illustrated schematically and non-limitingly. The figures are not necessarily drawn to scale, and some layer structures may be omitted as needed. The properties and functions of the layers in device 100, as well as exemplary materials, are described in more detail in columns 6-10 of U.S. Patent 7,279,704B2, the entire contents of which are incorporated herein by reference.

[0022] There are numerous examples of each of these layers. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is also incorporated herein by reference in its entirety.

[0023] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0024] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0025] In one embodiment, two or more OLED units can be connected in series to form a series OLED, such as... Figure 2 The tandem organic light-emitting device 500 is illustrated schematically and non-limitingly. OLEDs can also be equipped with an encapsulation layer, such as... Figure 3 An organic light-emitting device 600 is shown schematically and non-limitingly, which is related to... Figure 2The difference lies in the fact that an encapsulation layer 102 may also be included above the cathode 290 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED element. Multilayer thin-film encapsulation is described in U.S. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0026] Components manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units). Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, tablet phones, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0027] The materials and structures described in this article can also be used in other organic electronic components listed above.

[0028] As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. When the first layer is described as being "disposed" on the second layer, the first layer is positioned further from the substrate. Unless it is specified that the first layer "contacts" the second layer, other layers may exist between the first and second layers. For example, even if various organic layers exist between the cathode and anode, the cathode may still be described as being "disposed" on the anode.

[0029] As used herein, “solution-handleable” means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0030] When a ligand is believed to directly contribute to the photosensitivity of the emitting material, the ligand can be called "photosensitive." When a ligand is believed not to contribute to the photosensitivity of the emitting material, the ligand can be called "auxiliary," but auxiliary ligands can alter the properties of photosensitivity ligands.

[0031] Definition of the term "substituent group"

[0032] Halogens or halides: as used herein, include fluorine, chlorine, bromine, and iodine.

[0033] Alkyl groups include straight-chain and branched alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Additionally, alkyl groups may optionally be substituted. The carbon atoms in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, and neopentyl are preferred.

[0034] Cycloalkyl groups, as used herein, comprise cyclic alkyl groups. Preferred cycloalkyl groups are those containing 3 to 40 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Furthermore, the cycloalkyl group may optionally be substituted. The carbon atoms in the ring may be substituted with other heteroatoms.

[0035] Alkenes, as used herein, encompass straight-chain, branched, and cyclic olefin groups. Preferred alkenes are those containing 2 to 40 carbon atoms. Examples of alkenes include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl. Furthermore, alkenes may be optionally substituted.

[0036] Aryl or aromatic groups, as used herein, are considered in both non-fused and fused systems. Preferred aryl groups are those containing 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, leucine, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. Furthermore, the aryl group may optionally be substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-triphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methyldiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-dimethylyl, 3,4-dimethylyl, 2,5-dimethylyl, methyltrimethylyl, and m-tetraphenyl.

[0037] Heterocyclic groups or heterocycles, as used herein, refer to both aromatic and non-aromatic cyclic groups. Isoaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, and sulfur. Heterocyclic groups can also be aromatic heterocyclic groups having at least one heteroatom selected from nitrogen, oxygen, sulfur, and selenium atoms.

[0038] Heterocyclic aryl groups, as used herein, include both non-fused and fused heteroaryl groups that may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing 2 to 60 carbon atoms, more preferably 3 to 20 carbon atoms, and even more preferably 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzothiophene pyridine, thiophene dipyridine, benzothiophene pyridine, thiophene dipyridine, benzoselenophene pyridine, selenobenzobispyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0039] Alkoxy groups are represented by -O-alkyl groups, and examples and preferred examples of alkyl groups are the same as described above. Examples of alkoxy groups having 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, include methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy. Alkoxy groups having 3 or more carbon atoms can be linear, cyclic, or branched.

[0040] Aryl groups are represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of aryl groups having 6 to 60 carbon atoms include phenoxy and biphenyloxy groups.

[0041] Aryl groups, as used herein, are alkyl groups having an aryl substituent. Additionally, aryl groups may optionally be substituted. Examples of aryl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-2-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred.

[0042] In this specification, the term "substituted or unsubstituted" refers to a substance selected from hydrogen, deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidine, hydrazine, hydrazone, carboxyl or its carboxylate, sulfonic acid or its sulfonate, phosphate or its phosphate, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 cycloalkyl, C3-C 60 Cycloalkenyl, C6-C 60 Aryl, C6-C 60 Aryloxy group, C6-C 60 Aryl sulfide groups and C2-C 60 The heterocyclic aryl group is substituted or unsubstituted by one or more substituents, or is substituted or unsubstituted by a substituent formed by linking two or more substituents of the substituents exemplified above.

[0043] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0044] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance the efficiency and stability of the components.

[0045] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum range of available substitutions.

[0046] According to one embodiment of the present invention, a compound is disclosed:

[0047]

[0048] Among them, X 1 X 2 X 3 X 4 Each independently selected from CR 0 Or N, and in X 1 X 2 X 3 X 4 At least two of them are N;

[0049] R 1 R 2 Each time they appear, the same or different ones represent electron-withdrawing groups;

[0050] R 0 R 3 R 4 Each is independently selected from hydrogen, deuterium, halogen, nitrile group, substituted or unsubstituted C1-C. 40 Alkyl, substituted or unsubstituted C3-C 40 Branched alkyl or cycloalkyl groups, substituted or unsubstituted C1-C 40 heteroalkyl, substituted or unsubstituted C2-C 40 alkenyl, substituted or unsubstituted C6-C 60 aryl, substituted or unsubstituted C6-C 60 aryloxy, substituted or unsubstituted C7-C 60 Aryl, substituted or unsubstituted C3-C 40 alkylsilyl, substituted or unsubstituted C6-C60 arylsilyl, substituted or unsubstituted, having C0-C 40 The amino group, or the substituted or unsubstituted C2-C 60 The group consisting of heterocyclic aryl, acyl, carbonyl, carboxylic acid, ester, isonitrile, thio, sulfinyl, sulfonyl, phosphinyl, and phosphoxy groups, wherein two or more adjacent groups may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, the formed rings containing or not containing one or more heteroatoms N, P, B, O, or S.

[0051] According to embodiments of the present invention, the compound is as shown in Formula 1 or Formula 2:

[0052]

[0053] Among them, R 0 R 1 R 2 R 3 R 4 The meaning is the same as the definition above.

[0054] Furthermore, the R 0 R 3 R 4 Each of the following groups, individually or otherwise, is selected from: hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, pentafluoroethyl, pentafluoroethoxy, cyano, nitro, methanesulfonyl, trifluoromethanesulfonyl, trifluoroacetyl, trifluoromethylthio, pentafluorothio, pyridyl, fluorophenyl, difluorophenyl, trifluorophenyl, tetrafluorophenyl, pentafluorophenyl, cyanophenyl, trifluoromethylphenyl, trifluoromethoxyphenyl, pentafluoroethylphenyl, pentafluoroethoxyphenyl, nitrophenyl, methanesulfonylphenyl, trifluoromethanesulfonylphenyl, trifluoromethylthiophenyl, pentafluorothiophenyl, cyanofluorophenyl, cyanodifluorophenyl, cyanotrifluorophenyl, cyanotetrafluorophenyl, pyrimidinyl, triazine, 2,6-dimethyl-1,3,5-triazine, 2,6-di(trifluoromethyl)-1,3,5-triazine, and combinations thereof.

[0055] Furthermore, the R 1 R 2 Each is independently selected from the group consisting of trifluoromethyl, cyano, pentafluorophenyl, pyridyl, and cyanotetrafluorophenyl.

[0056] According to another embodiment of the present invention, the R 1 R 2 Each is independently selected from trifluoromethyl or cyano groups.

[0057] According to a preferred embodiment of the present invention, the compound is selected from the group consisting of formulas CJHM383 to CJHM606:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] The present invention also provides an organic electroluminescent material comprising a compound represented by the above general formula (I).

[0065] According to one embodiment of the present invention, the hole injection layer is in contact with the anode.

[0066] According to one embodiment of the present invention, the hole injection layer comprises a compound represented by the general formula (I).

[0067] According to one embodiment of the present invention, the hole injection layer is composed solely of a compound represented by the general formula (I).

[0068] According to one embodiment of the present invention, the hole injection layer further comprises an aromatic amine compound.

[0069] According to one embodiment of the present invention, the organic electroluminescent element further includes a light-emitting layer.

[0070] The materials described in this invention for specific layers in organic light-emitting elements can be used in combination with a variety of other materials present in the element. These combinations of materials are described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0071] Materials described herein for use in specific layers of organic light-emitting elements can be used in combination with a variety of other materials present in said element. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of host layers, transport layers, barrier layers, injection layers, electrodes, and other possible layers. These combinations of materials are described in detail in paragraphs 0080-0101 of patent application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0072] The present invention also provides an organic electroluminescent element comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode; wherein at least one layer of the organic layer comprises a compound of formula (I) with pyrimidine fluorene as the parent nucleus.

[0073] The organic electroluminescent element comprises a cathode, an anode, and at least one emitting layer. In addition to these layers, it may also comprise other layers, such as, in each case, one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers, and / or charge generation layers. An intermediate layer having, for example, exciton blocking functionality may also be introduced between two emitting layers. However, it should be noted that each of these layers is not necessarily required. The organic electroluminescent device described herein may comprise one emitting layer, or it may comprise multiple emitting layers. That is, various luminescent compounds capable of emitting light are used in the emitting layers. A system having three emitting layers is particularly preferred, wherein the three layers can exhibit blue, green, and red light emission. If more than one emitting layer exists, according to the invention, at least one of these layers comprises a compound of the invention.

[0074] Furthermore, the organic electroluminescent element according to the present invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, that is, the light-emitting layer is directly adjacent to the hole injection layer or the anode, and / or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.

[0075] In the other layers of the organic electroluminescent element according to the invention, particularly in the hole injection and hole transport layers and in the electron injection and electron transport layers, all materials can be used in accordance with the manner commonly used in the prior art. Those skilled in the art will therefore be able to use all materials known about organic electroluminescent elements in combination with the light-emitting layers according to the invention without inventive effort.

[0076] Furthermore, the following organic electroluminescent elements are preferred, wherein one or more layers are applied by means of a sublimation method, wherein in a vacuum sublimation apparatus at a temperature below 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may be even lower, for example, below 10 Pa. -7 Pa.

[0077] Similarly, the following organic electroluminescent elements are preferred, wherein one or more layers are applied by means of organic vapor deposition or by means of carrier gas sublimation, wherein, in 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, in which the material is applied directly through a nozzle and is therefore structured.

[0078] Furthermore, the following organic electroluminescent elements are preferred, which produce one or more layers from solution, for example by spin coating, or by any desired printing method such as screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, inkjet printing, or nozzle printing. Soluble compounds, for example, obtained through appropriate substitution, are also preferred. These methods are particularly suitable for oligomers, dendritic macromolecules, and polymers. Additionally, mixing methods are feasible, in which one or more layers are applied from solution and one or more additional layers are applied by vapor deposition.

[0079] The present invention also provides a series organic electroluminescent element, comprising an anode, a cathode, and a plurality of stacked layers disposed between the anode and the cathode, each stacked layer comprising at least one light-emitting layer, and a charge-generating layer disposed between each two adjacent stacked layers, the charge-generating layer comprising a p-type charge-generating layer and an n-type charge-generating layer, wherein the p-type charge-generating layer comprises a compound represented by the general formula (I) described above.

[0080] Furthermore, in the organic electroluminescent element according to the present invention, the compound represented by the general formula (I) has a mass percentage content of 1% to 100% in the hole injection layer or charge generation layer.

[0081] These methods are generally known to those skilled in the art, and they can be applied without creative effort.

[0082] Therefore, the present invention also relates to a method of manufacturing an organic electroluminescent element according to the invention, wherein at least one layer is applied by means of a sublimation method, and / or by means of an organic vapor deposition method or by means of carrier gas sublimation, and / or at least one layer is applied from a solution by spin coating or by means of a printing method.

[0083] Furthermore, the present invention relates to compounds comprising at least one of the compounds of the invention as described above. The same preferred embodiments as noted above with respect to organic electroluminescent elements apply to the compounds of the present invention. In particular, the compounds may also preferably contain other compounds. Processing the compounds according to the invention from the liquid phase, for example by spin coating or printing methods, requires formulations of the compounds according to the invention. These formulations may be, for example, solutions, dispersions, or emulsions. For this purpose, mixtures of two or more solvents may be preferred. Suitable and preferred solvents include, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, naphthalene, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenazine, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methyl anisole, 4-methyl anisole, 3,4-dimethyl anisole, 3,5-dimethyl anisole, acetophenone, α-terpenes. Alcohol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-methylisopropylbenzene, phenethyl ether, 1,4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentabenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, or mixtures of these solvents.

[0084] A consumer product comprising the above-described organic electroluminescent element or the above-described tandem organic electroluminescent element. In some embodiments, the consumer product may be one of the following: flat panel display, computer monitor, medical monitor, television set, signboard, lamp for internal or external lighting and / or signaling, head-up display, fully transparent or partially transparent display, flexible display, laser printer, telephone, cellular phone, tablet computer, phablet, personal digital assistant (PDA), wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay with a diagonal of less than 2 inches, 3D display, virtual reality or augmented reality display, vehicle, video wall comprising multiple displays tiled together, theater or stadium screen, phototherapy device, and signage.

[0085] In addition, unless otherwise specified, all raw materials used in this invention can be obtained commercially available. Any range described in this invention includes the end value and any value between the end values, as well as any subrange formed by the end value or any value between the end values.

[0086] The beneficial effects achieved by this invention are as follows:

[0087] The compound with dipyrimidine fluorene as the parent core, or the material composed of a compound with dipyrimidine fluorene as the parent core, as shown in Formula (I) provided by the present invention, can reduce the voltage of OLED devices and improve the efficiency and lifespan of the devices.

[0088] In the description of this invention, unless otherwise stated, "a plurality of" means two or more; the terms "upper," "lower," etc., indicate the orientation or positional relationship based on the orientation or positional relationship shown in the drawings, and are only for the convenience of describing the invention and simplifying the description, and do not indicate or imply that the device or element referred to must have a specific orientation, or be constructed and operated in a specific orientation, and therefore should not be construed as a limitation of the invention.

[0089] Unless otherwise specified, the experimental methods used in the following embodiments are conventional methods. Unless otherwise specified, the experimental materials and related equipment used in the following embodiments are commercially available, and all percentages are by mass.

[0090] The following embodiments use the following testing instruments and methods for performance testing of OLED materials and components:

[0091] OLED component performance testing conditions:

[0092] Luminosity and chromaticity coordinates: tested using a PhotoResearch PR-715 spectral scanner;

[0093] Current density and turn-on voltage: tested using a Keithley 2420 digital source meter;

[0094] Power efficiency: Tested using NEWPORT 1931-C.

[0095] Compound Synthesis Examples

[0096] Example 1

[0097] The preparation method of compound CJHM389 includes the following steps:

[0098] Step 1: Preparation of compound Int-1

[0099]

[0100] 40.0 mmol of 1,2-cyclopentanedione was dissolved in 50 mL of N,N-dimethylformamide dimethyl acetal (DMF-DMA), and the mixture was heated to reflux and stirred for 5 hours. The mixture was then concentrated under reduced pressure to dryness to give compound Int-1, a yellow liquid with a yield of 100%. No purification was required, and it was used directly in the next step of the reaction.

[0101] Step 2: Preparation of compound Int-2

[0102]

[0103] 30.0 mmol of Int-1 and 100 g of urea were mixed and reacted under nitrogen protection at 150 °C with stirring for 2 hours. The mixture was then cooled to 90 °C, and 150 mL of 5% sodium hydroxide aqueous solution was added dropwise. The mixture was stirred for 1 hour and then cooled to room temperature. The mixture was filtered, and the filter cake was washed with water and ethanol and dried to give compound Int-2 as a white solid with a yield of 85%.

[0104] Step 3: Preparation of compound Int-3

[0105]

[0106] 20.0 mmol of Int-2, 60.0 mmol of potassium persulfate and 20.0 mmol of copper sulfate hydrate were dispersed in 50 mL of acetonitrile and 50 mL of water. The mixture was heated to reflux and stirred for 1 hour. After cooling to room temperature, 50 mL of water was added, and the mixture was extracted with dichloromethane. The organic phase was dried, concentrated under reduced pressure, and then 50 mL of water was added. The mixture was stirred and filtered. The filter cake was washed with water and ethanol to give compound Int-3 as a white solid with a yield of 92%.

[0107] Step 4: Preparation of compound Int-4

[0108]

[0109] Under nitrogen protection, 30.0 mmol of Int-3 was dissolved in 50 mL of phosphorus oxychloride, heated to reflux and stirred for 5 hours, cooled to room temperature, 100 g of crushed ice was added, stirred and filtered, and the filter cake was washed with ice water to obtain compound Int-4, a white solid, with a yield of 90%.

[0110] Step 5: Preparation of compound Int-5

[0111]

[0112] Under nitrogen protection, 20.0 mmol of Int-4 was dissolved in 60 mL of toluene, followed by the addition of 60.0 mmol of potassium phosphate hydrate, 48.0 mmol of pentafluorophenylboronic acid, 0.01 mmol of Pd132, and 2.0 mmol of tetrabutylammonium bromide, 30 mL of ethanol, and 20 mL of water. The mixture was heated to reflux and stirred for 15 hours, then cooled to room temperature. 50 mL of ice water was added, and the organic phase was separated. The aqueous phase was extracted with dichloromethane, and the organic phases were combined, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. Ethanol was added, stirred, and dispersed, and then filtered to give compound Int-5 as a yellow solid with a yield of 74%.

[0113] Step 6: Preparation of compound CJHM389

[0114]

[0115] Under nitrogen protection, 10.0 mmol of Int-5, 30.0 mmol of malononitrile, and 200 mL of chlorobenzene were mixed and cooled to 0 °C. 100.0 mmol of titanium tetrachloride and 200.0 mmol of pyridine were added, and the mixture was heated to reflux and stirred for 24 hours. After cooling to room temperature, 500 mL of petroleum ether was added, and the mixture was filtered. The filter cake was washed with petroleum ether and then with dichloromethane-petroleum ether to give compound CJHM389. After sublimation purification, a white solid was given. Yield: 70–75%. MS (TOF-SIMS) m / z: 564.01. 1 HNMR (400MHz, CDCl3), δ=9.75 (s, 2H).

[0116] Example 2

[0117] The preparation method of compound CJHM427 includes the following steps:

[0118] Step 1: Preparation of compound Int-6

[0119]

[0120] 40.0 mmol of 1,3-cyclopentanedione was dissolved in 80 mL of toluene, and then 88.0 mmol of DMF-DMA was added. The mixture was heated to reflux and stirred for 12 hours. The solution was then concentrated under reduced pressure to dryness to give compound Int-6, a yellow liquid with a yield of 100%. No purification was required, and it was used directly in the next step of the reaction.

[0121] Step 2: Preparation of compound Int-7

[0122]

[0123] 30.0 mmol of Int-6 and 150.0 mmol of urea were dissolved in 120 mL of glacial acetic acid. The mixture was heated to reflux and stirred for 5 hours. After cooling to room temperature, the mixture was concentrated to dryness under reduced pressure. 200 mL of 5% sodium hydroxide aqueous solution was added, and the mixture was heated to reflux. After cooling to room temperature, the mixture was filtered, and the filter cake was washed with water to give compound Int-7 as a yellow solid. Yield: 52-56%.

[0124] Step 3: Preparation of compound Int-8

[0125]

[0126] Following the synthesis method of step 3 in Example 1, only Int-2 in step 3 of Example 1 was replaced with Int-7 to obtain compound Int-8, a white solid with a yield of 90%.

[0127] Step 4: Preparation of compound Int-9

[0128]

[0129] Following the synthesis method in step four of Example 1, only Int-3 in step four of Example 1 was replaced with Int-8 to obtain compound Int-9, a yellow solid, with a yield of 93%.

[0130] Step 5: Preparation of compound Int-10

[0131]

[0132] Following the synthesis method in step 5 of Example 1, only Int-4 in step 5 of Example 1 was replaced with Int-9 to obtain compound Int-10, a yellow solid, with a yield of 73%.

[0133] Step 6: Preparation of compound CJHM427

[0134]

[0135] Following the synthetic method of step 6 in Example 1, except that Int-5 was replaced with Int-10, compound CJHM427 was prepared. After sublimation purification, a white solid was obtained, with a yield of 60-65% and MS (TOF-SIMS) m / z of 564.02. 1 HNMR (400MHz, CDCl3), δ=10.26 (s, 1H); 9.37 (s, 1H).

[0136] Following a similar synthetic method to the above embodiments, the following compounds were prepared:

[0137]

[0138]

[0139]

[0140] Example 3

[0141] The preparation method of compound CJHM554 includes the following steps:

[0142] Step 1: Preparation of compound Int-11

[0143]

[0144] Under nitrogen protection, 100 mL of anhydrous ethanol was cooled to 0 °C, and 66.0 mmol of metallic sodium was added in portions. The mixture was stirred until the sodium lumps disappeared. 20.0 mmol of 1,2-cyclopentanedione and 60.0 mmol of diethyl formate were added dropwise. The mixture was heated to room temperature and stirred for 15 hours. The mixture was concentrated to dryness under reduced pressure, and 100 mL of water was added. The solution was adjusted to acidity with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was collected, washed with saturated brine, dried, filtered, and the filtrate was concentrated and dried under reduced pressure to give compound Int-11, a yellow liquid with a yield of 100%. No purification was required, and it was used directly in the next reaction.

[0145] Step 2: Preparation of compound Int-12

[0146]

[0147] Following the synthesis method of step 2 in Example 1, Int-1 in step 2 of Example 1 was replaced with Int-11 to prepare compound Int-12, a white solid with a yield of 90-95%.

[0148] Step 3: Preparation of compound Int-13

[0149]

[0150] Following the synthesis method in step 3 of Example 1, only Int-2 in step 3 of Example 1 was replaced with Int-12 to prepare compound Int-13, a white solid with a yield of 85-90%.

[0151] Step 4: Preparation of compound Int-14

[0152]

[0153] Following the synthesis method in step four of Example 1, except that Int-3 in step four of Example 1 was replaced with Int-13, compound Int-14 was prepared as a yellow solid with a yield of 90-95%.

[0154] Step 5: Preparation of compound Int-15

[0155]

[0156] Under nitrogen protection, 20.0 mmol of Int-14 was dissolved in 80 mL of THF, followed by the addition of 200.0 mmol of potassium phosphate hydrate, 100.0 mmol of 4-cyano-tetrafluorophenylboronic acid, 0.01 mmol of Pd132, and 2.0 mmol of tetrabutylammonium bromide, and then 40 mL of water. The mixture was heated to reflux and stirred for 15 hours, then cooled to room temperature, and 50 mL of ice water was added. The mixture was filtered, and the filter cake was washed with ethanol to obtain compound Int-15 as a yellow solid, with a yield of 56%.

[0157] Step 6: Preparation of compound CJHM554

[0158]

[0159] Following the synthesis method in step 6 of Example 1, except that Int-5 in step 6 of Example 1 was replaced with Int-15, compound CJHM554 was prepared. After sublimation and purification, a white solid was obtained with a yield of 50-55% and MS (TOF-SIMS) m / z of 924.00.

[0160] Example 4

[0161] The preparation method of compound CJHM440 includes the following steps:

[0162] Step 1: Preparation of compound Int-16

[0163]

[0164] Following the synthesis method in the first step of Example 3, sub-1 in the first step of Example 3 was replaced with sub-2, and diethanol formate was replaced with diethyl oxalate to prepare compound Int-16, a yellow liquid with a yield of 100%. No purification was required, and it was directly used in the next reaction.

[0165] Step 2: Preparation of compound Int-17

[0166]

[0167] 30.0 mmol of Int-16 and 150.0 mmol of urea were dissolved in 80 mL of glacial acetic acid. The mixture was heated to 80 °C and stirred for 15 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to dryness. 200 mL of 5% sodium hydroxide aqueous solution was added, and the mixture was filtered. The filter cake was washed with water to obtain compound Int-17, a white solid with a yield of 80-85%.

[0168] Step 3: Preparation of compound Int-18

[0169]

[0170] 20.0 mmol of Int-17 was dissolved in 50 mL of phosphorus oxychloride, heated to reflux and stirred for 5 hours, cooled to room temperature, concentrated under reduced pressure to dryness, 200 g of crushed ice was added, stirred and filtered, and the filter cake was washed with ice water to obtain compound Int-18, a yellow solid, with a yield of 90-95%.

[0171] Step 4: Preparation of compound Int-19

[0172]

[0173] 20.0 mmol of Int-18 and 60.0 mmol of 2-iodobenzoic acid were dissolved in 50 mL of DMSO. The mixture was heated to 80 °C and stirred for 10 hours. After cooling to room temperature, the reaction solution was poured into 200 mL of ice-water solution, filtered, and the filter cake was washed with water to obtain compound Int-19, a white solid, with a yield of 70–75%.

[0174] Step 5: Preparation of compound Int-20

[0175]

[0176] Following the synthesis method in step 5 of Example 1, only Int-4 in step 5 of Example 1 was replaced with Int-19 to obtain compound Int-20, a yellow solid, with a yield of 78%.

[0177] Step 6: Preparation of compound CJHM440

[0178]

[0179] Following the synthesis method in step 6 of Example 1, except that Int-5 in step 6 of Example 1 was replaced with Int-20, compound CJHM440 was prepared. After sublimation and purification, a white solid was obtained with a yield of 70-75% and MS (TOF-SIMS) m / z of 614.01.

[0180] Following a similar synthetic method to the above embodiments, the following compounds were prepared:

[0181]

[0182]

[0183]

[0184]

[0185] Example 5

[0186] The preparation of compound CJHM393 includes the following steps:

[0187] Step 1: Preparation of compound Int-21

[0188]

[0189] 20.0 mmol of Int-11, 48.0 mmol of sub-3 and 48.0 mmol of sodium hydroxide were dissolved in 100 mL of anhydrous ethanol. The mixture was heated to reflux and stirred for 10 hours. After cooling to room temperature, the mixture was filtered, and the filter cake was washed with ethanol to give compound Int-21 as a yellow solid with a yield of 80-85%.

[0190] Step 2: Preparation of compound Int-22

[0191]

[0192] 20.0 mmol of Int-21 was dissolved in 20 mL of dichloromethane, cooled to 0 °C, and 80.0 mmol of diethylaminotrifluoride (DAST) was added dropwise. The mixture was stirred for 1 hour, then heated to room temperature and stirred for 15 hours. 50 mL of ice water was added dropwise, the organic phase was separated, washed with water, dried, filtered, and the filtrate was concentrated to dryness under reduced pressure. The filtrate was purified by silica gel column chromatography to give compound Int-22 as a yellow solid, with a yield of 90–95%.

[0193] Step 3: Preparation of compound Int-23

[0194]

[0195] Following the synthesis method of step four in Example 4, only Int-18 in step four of Example 4 was replaced with Int-22 to obtain compound Int-23, a yellow solid, with a yield of 70% to 75%.

[0196] Step 4: Preparation of compound CJHM393

[0197]

[0198] Following the synthetic method of step 6 in Example 1, except that Int-5 was replaced with Int-23, compound CJHM393 was prepared. After sublimation purification, a white solid was obtained, with a yield of 70-75% and MS (TOF-SIMS) m / z of 528.03. 1 HNMR (400MHz, CDCl3), δ=8.12~8.10 (m, 4H).

[0199] Following a similar synthetic method to the above embodiments, the following compounds were prepared:

[0200]

[0201]

[0202]

[0203] Example 6

[0204] The preparation of compound CJHM542 includes the following steps:

[0205] Step 1: Preparation of compound Int-24

[0206]

[0207] Following the synthesis method in step one of Example 5, except that sub-3 in step one of Example 5 was replaced with sub-4, compound Int-24 was obtained, a yellow solid, with a yield of 70% to 75%.

[0208] Step 2: Preparation of compound Int-25

[0209]

[0210] Following the synthesis method in step four of Example 1, only Int-3 in step four of Example 1 was replaced with Int-24 to obtain compound Int-25, a yellow solid, with a yield of 90%.

[0211] Step 3: Preparation of compound Int-26

[0212]

[0213] Following the synthesis method of step four in Example 4, only Int-18 in step four of Example 4 was replaced with Int-25 to obtain compound Int-26, a yellow solid, with a yield of 70% to 75%.

[0214] Step 4: Preparation of compound Int-27

[0215]

[0216] Under nitrogen protection, 20.0 mmol of Int-26 was dissolved in 80 mL of THF, followed by the addition of 80.0 mmol of potassium phosphate hydrate, 48.0 mmol of 3,4,5-trifluorophenylboronic acid, 0.01 mmol of Pd132, and 2.0 mmol of tetrabutylammonium bromide, and then 40 mL of water. The mixture was heated to reflux and stirred for 15 hours, then cooled to room temperature, and 50 mL of ice water was added. The mixture was filtered, and the filter cake was washed with water and then with ethanol to obtain compound Int-27, a yellow solid, with a yield of 67%.

[0217] Step 5: Preparation of compound CJHM542

[0218]

[0219] Following the synthetic method of step 6 in Example 1, except that Int-5 was replaced with Int-27, compound CJHM542 was prepared. After sublimation purification, a white solid was obtained, with a yield of 70-75% and MS (TOF-SIMS) m / z of 824.02. 1 HNMR (400MHz, CDCl3), δ=7.38~7.34 (m, 4H).

[0220] Following a similar synthetic method to the above embodiments, the following compounds were prepared:

[0221]

[0222]

[0223]

[0224]

[0225] Those skilled in the art should understand that the above preparation methods are merely exemplary examples, and they can obtain other compound structures of the present invention by improving them.

[0226] Light-emitting element embodiment

[0227] First, the glass substrate coated with an ITO conductive layer was ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonically treated in an acetone / ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dry, irradiated with a UV cleaner for 10 minutes, and bombarded with a low-energy cation beam. Then, the treated ITO glass substrate was placed on a support and put into a vacuum chamber, and the vacuum was evacuated to less than 1 × 10⁻⁶. -5 Pa, with The specified organic layers are sequentially vacuum-deposited at a rate of / second.

[0228] 1) The compound (Formula I) of the above embodiment of the present invention, as a dopant material, and HI01, as the host material, are deposited on the above-mentioned ITO anode layer film. The compound (Formula I) of the present invention accounts for 3% of the mass of HI01 and serves as the hole injection layer (HIL) of the element. The thickness of the deposited film is...

[0229] 2) HT010 is further deposited on the aforementioned hole injection layer to form a hole transport layer (HTL), with a film thickness of [missing information].

[0230] 3) GH02 as the host material and GD11 as the dopant material are further deposited on the hole transport layer. GD11 accounts for 5% of the mass of GH02. This serves as the organic light-emitting layer for the device. The thickness of the deposited organic light-emitting layer is [missing information].

[0231] 4) A mixture of ET25 and LiQ is deposited on the organic light-emitting layer, with an ET25:LiQ mass ratio of 1:1, as the electron transport layer of the device. The deposited film thickness is [missing information].

[0232] 5) A LiF layer is deposited on top of the electron transport layer as an electron injection layer, with a film thickness of [missing information].

[0233] 6) Aluminum is deposited on top of the electron injection layer as the cathode layer of the component, with a film thickness of [missing information]. The component is then transferred to a glove box and sealed with a glass cover and desiccant to obtain the OLED component provided by the present invention.

[0234] The material structure used in the component is as follows:

[0235]

[0236] The structure of the prepared organic light-emitting device 100 is as follows: Figure 1 As shown, the substrate is 101, the anode is 110, the hole injection layer is 120, the hole transport layer is 130, the electron blocking layer is 140, the light-emitting layer is 150, the hole blocking layer is 160, the electron transport layer is 170, the electron injection layer is 180, and the cathode is 190.

[0237] A tandem organic light-emitting device 500 was prepared in a similar manner, and its structure is as follows: Figure 3 As shown, the device includes a substrate 101, an anode 110, a first unit 100, a charge generation layer 300, a second unit 200, and a cathode 290. The first unit 100 includes a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, and an electron transport layer 170. The second unit 200 includes a hole injection layer 220, a hole transport layer 230, an electron blocking layer 240, a light-emitting layer 250, a hole blocking layer 260, an electron transport layer 270, and an electron injection layer 280. The charge generation layer 300 includes an N-type charge generation layer 310 and a P-type charge generation layer 320.

[0238] This embodiment can prepare another tandem organic light-emitting device 600, the structure of which is as follows: Figure 3As shown, the device includes a substrate 101, an anode 110, a first unit 100, a charge generation layer 300, a second unit 200, an encapsulation layer 102, and a cathode 290. The first unit 100 includes a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, and an electron transport layer 170. The second unit 200 includes a hole injection layer 220, a hole transport layer 230, an electron blocking layer 240, a light-emitting layer 250, a hole blocking layer 260, an electron transport layer 270, and an electron injection layer 280. The charge generation layer 300 includes an N-type charge generation layer 310 and a P-type charge generation layer 320.

[0239] Comparative Example 1

[0240] Following the same steps as described above, replace the compound (Formula I) of the present invention in step 1) with H1 to obtain comparative element 1;

[0241]

[0242] The organic electroluminescent elements prepared by the above process were subjected to the following performance tests:

[0243] The driving voltage, current efficiency, and lifetime of the organic electroluminescent elements prepared in the above embodiments and Comparative Example 1 were measured using a digital source meter and a luminance meter. Specifically, the voltage was increased at a rate of 0.1V per second, and the luminance of the organic electroluminescent element was measured when it reached 1000 cd / m². 2 The voltage at that time is the driving voltage, and the current density at that time is measured simultaneously; the ratio of brightness to current density is the current efficiency; the LT95% lifespan test is as follows: using a luminance meter at 1000 cd / m² 2 At a constant current under the given brightness, the brightness decay of the organic electroluminescent element was measured to be 950 cd / m². 2 The time is in hours. The data listed in Table 1 are relative to Comparison Element 1.

[0244] Table 1 Component Data

[0245]

[0246]

[0247]

[0248]

[0249]

[0250] As shown in Table 1 above, the compounds of the present invention, when used as materials for organic light-emitting elements in the hole injection layer, exhibit superior performance compared to the comparative compound H1 in various aspects. For example, the embodiments of the present invention have a lower driving voltage than comparative example 1, indicating that hole injection using the compounds of the present invention is much more efficient and energy-saving than the comparative compounds, and has higher current efficiency and longer device life.

[0251] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some of the technical features; and these modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. A dipyrimidine fluorene compound, characterized in that, The compounds are selected from the group consisting of formulas CJHM383 to CJHM606:

2. An organic electroluminescent material, characterized in that, It contains the compound as described in claim 1.

3. An organic electroluminescent element, characterized in that, include: An anode, a cathode, and a hole injection layer and a charge generation layer disposed between the anode and the cathode, wherein the hole injection layer or the charge generation layer comprises the compound of claim 1.

4. The organic electroluminescent element according to claim 3, characterized in that, The hole injection layer also contains a triarylamine compound.

5. A series-connected organic electroluminescent element, characterized in that, include: An anode, a cathode, and a plurality of stacked layers disposed between the anode and the cathode, each stacked layer including at least one light-emitting layer, and a charge-generating layer disposed between every two adjacent stacked layers, the charge-generating layer including a p-type charge-generating layer and an n-type charge-generating layer, wherein the p-type charge-generating layer comprises the compound as described in claim 1.

6. The organic electroluminescent element according to any one of claims 4-5, characterized in that, The compound has a mass percentage content of 1% to 100% in the hole injection layer or charge production layer.

7. A consumer product comprising the organic electroluminescent element as described in any one of claims 4 to 5.

Images